The present invention relates to the use of oxathiazolones in the antimicrobial treatment of surfaces.
The oxathiazolones used according to the invention correspond to formula 
wherein
R1, is C1-C16alkyl, C2-C16alkenyl or C5-C8cycloalkyl, each unsubstituted or substituted by halogen, xe2x80x94CN, xe2x80x94NO2, xe2x80x94Cxe2x95x90O, xe2x80x94Cxe2x95x90S, xe2x80x94NR2, xe2x80x94OR3, xe2x80x94SR4, xe2x80x94SO2R5, xe2x80x94COOR6 or by a 1,3,4-oxathiazol-2-one radical; C6-C10aryl unsubstituted or substituted by one or more C1-C5alkyl, C6-C10aryl, halogen, hydroxy, acyl, xe2x80x94CN, xe2x80x94CF3, xe2x80x94NO2, xe2x80x94NR2, xe2x80x94OR3, xe2x80x94SR4, xe2x80x94SO3H, xe2x80x94SO2R5, xe2x80x94COOR6 substituents or by a 1,3,4-oxathiazol-2-one radical; or a 5- or 6-membered heterocyclic radical;
R2 and R3 are each independently of the other hydrogen; C1-C5alkyl; C6-C10aryl, or acyl;
R4 is hydrogen; C1-C5alkyl; or C6-C10aryl;
R5 is C1-C5alkyl; or C6-C10aryl;
R6 is hydrogen; C1-C5alkyl; or C6-C10aryl.
C1-C16Alkyl are straight-chain or branched alkyl radicals, e.g. methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, amyl, isoamyl or tert-amyl, heptyl, octyl, isooctyl, nonyl, decyl, undecyl, dodecyl, tetradecyl, pentadecyl or hexadecyl.
C2-C16Alkenyl is e.g. allyl, methallyl, isopropenyl, 2-butenyl, 3-butenyl, isobutenyl, n-penta-2,4-dienyl, 3-methyl-but-2-enyl, n-oct-2-enyl, n-dodec-2-enyl, 3,6,8-decatrienyl or isododecenyl.
C6-C10Aryl can be a mono- or bi-cyclic aromatic radical, e.g. phenyl or naphthyl.
C5-C8Cycloalkyl can be cyclopentyl, cycloheptyl, cyclooctyl or preferably cyclohexyl.
Examples of 6-membered heterocyclic radicals are pyranyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, piperazinyl, indolinyl and morpholinyl.
Examples of 5-membered heterocyclic radicals are thienyl, furyl, 2H-pyrrolyl, pyrrolyl, imidazolyl, pyrazolyl, isoxazolyl, furazanyl, pyrrolidinyl, pyrrolinyl, imidazolidinyl, pyrazolidinyl and pyrazolinyl.
The 5- or 6-membered heterocyclic radicals can be unsubstituted or substituted by halogen, such as chlorine or bromine, nitro, C1-C5alkyl or by C1-C5alkoxy.
According to the invention, preference is given to the use of compounds of formula (1) wherein
R1 is C1-C16alkyl unsubstituted or substituted by halogen, xe2x80x94CN, xe2x80x94NO2, xe2x80x94Cxe2x95x90O, xe2x80x94Cxe2x95x90S, xe2x80x94NR2, xe2x80x94OR3, xe2x80x94SR4, xe2x80x94SO2R5, xe2x80x94COOR6 or by a 1,3,4-oxathiazol-2-one radical; or C6-C10aryl unsubstituted or substituted by one or more C1-C5alkyl, C6-C10aryl, halogen, hydroxy, acyl, xe2x80x94CN, xe2x80x94CF3, xe2x80x94NO2, xe2x80x94NR2, xe2x80x94OR3, xe2x80x94SR4, xe2x80x94SO3H, xe2x80x94SO2R5, xe2x80x94COOR6 substituents or by a 1,3,4-oxathiazol-2-one radical; and
R2, R3, R4, R5 and R6 are as defined for formula (1).
Special preference is given to compounds of formula (1) wherein
R1 is C1-C16alkyl; especially C1-C12alkyl and more especially methyl or ethyl.
According to the invention, use is also preferably made of oxathiazolones of formula 
wherein
R7, R8 and R9 are each independently of the others hydrogen; halogen; hydroxy; or C1-C5alkyl.
Examples of compounds that can be used according to the invention correspond to formulae 
In formula (7), R=xe2x80x94CH3; or xe2x80x94(CH2)10CH3.
The compounds of formulae (1) to (8) are known in the literature. The compound of formula (9) is a new compound.
The preparation of the oxanilides used according to the invention is effected in accordance with known procedures by reacting a carboxylic acid amide of formula 
with chlorocarbonylsulfenic acid chloride, corresponding to formula 
in accordance with the following scheme: 
wherein R1 is as defined for formula (1).
The starting materials corresponding to formula (7) are known. Chlorocarbonylsulfenic acid chloride (compound of formula (11)) is a known reagent of organic chemistry.
The preparation process is preferably carried out without an acid acceptor but can also be carried out in the presence of a suitable acid acceptor. As such there come into consideration all customary organic and inorganic bases. These include, for example, alkaline earth metal and alkali metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates and hydrogen carbonates, e.g. sodium hydride, sodium amide, sodium methanolate, sodium ethanolate, potassium tert-butanolate, sodium hydroxide, potassium hydroxide, ammonium hydroxide, sodium acetate, potassium acetate, calcium acetate, ammonium acetate, sodium carbonate, potassium carbonate, sodium potassium carbonate or hydrogen carbonate, ammonium carbonate, and also tertiary amines, such as trimethylamine, triethylamine, tributylamine, N,N-dimethylaniline, N,N-dimethylbenzylamine, pyridine, N-methylpiperidine and N,N-dimethylaminopyridine.
The process is preferably carried out in the presence of a solvent. All customary organic solvents come into consideration for that purpose. These include especially aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, e.g. benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride, ethers, such as dimethyl ether, diethyl ether, dioxane, tetrahydrofuran and ethylene glycol dimethyl ether, ketones, such as acetone, butanone and methyl isobutyl ketone, nitriles, such as acetonitrile, propionitrile and benzonitrile; amides, such as N,N-dimethylformamide, N,N-dimethylacetamide, N,N-methylformanilide, N-methyl-pyrrolidone and hexamethylphosphoric acid triamide; esters, such as methyl acetate and ethyl acetate, sulfoxides, such as dimethyl sulfoxide, preferably hydrocarbons. Special preference is given to toluene and dioxane.
The reaction temperatures can be varied within a wide range. The operation is generally carried out at temperatures of from xe2x88x9210 to +180xc2x0 C., preferably at temperatures of from 20 to 130xc2x0 C.
The process is usually carried out under normal pressure, but may also be carried out at elevated or reduced pressure.
For carrying out the process, generally from 1 to 10 mol, preferably from 1.0 to 3 mol, of chlorocarbonylsulfenic acid chloride are used per mole of carboxylic acid amide of formula (10).
The oxathiazolones used according to the invention exhibit a pronounced antimicrobial action, especially against pathogenic gram-positive and gram-negative bacteria and also against bacteria of skin flora, e.g. Corynebacterium xerosis (bacteria that cause body odour), and also against yeasts and moulds. They are therefore especially suitable in the disinfection of the skin and mucosa and also of integumentary appendages (hair), more especially in the disinfection of the hands and of wounds.
They are therefore suitable as antimicrobial active ingredients in personal care preparations, for example shampoos, bath additives, hair-care products, liquid and solid soaps (based on synthetic surfactants and salts of saturated and/or unsaturated fatty acids), lotions and creams, deodorants, other aqueous or alcoholic solutions, e.g. cleansing solutions for the skin, moist cleansing cloths, oils or powders.
The invention therefore relates also to a personal care preparation comprising at least one compound of formula (1) as well as cosmetically tolerable carriers or adjuvants.
The personal care preparation according to the invention comprises from 0.01 to 15% by weight, preferably from 0.5 to 10% by weight, based on the total weight of the composition, of the oxathiazolone compound of formula (1), and cosmetically tolerable adjuvants.
Depending upon the form of the personal care preparation, it will comprise, in addition to the oxathiazolone compound of formula (1), further constituents, for example sequestering agents, colourings, perfume oils, thickening or solidifying (consistency regulator) agents, emollients, UV absorbers, skin-protective agents, antioxidants, additives that improve mechanical properties, such as dicarboxylic acids and/or Al, Zn, Ca and Mg salts of C14-C22fatty acids, and optionally preservatives.
The personal care preparation according to the invention may be formulated as a water-in-oil or oil-in-water emulsion, as an alcoholic or alcohol-containing formulation, as a vesicular dispersion of an ionic or non-ionic amphiphilic lipid, as a gel, a solid stick or as an aerosol formulation.
As a water-in-oil or oil-in-water emulsion, the cosmetically tolerable adjuvant contains preferably from 5 to 50% of an oily phase, from 5 to 20% of an emulsifier and from 30 to 90% water. The oily phase may contain any oil suitable for cosmetic formulations, e.g. one or more hydrocarbon oils, a wax, a natural oil, a silicone oil, a fatty acid ester or a fatty alcohol. Preferred mono- or poly-ols are ethanol, isopropanol, propylene glycol, hexylene glycol, glycerol and sorbitol.
Cosmetic formulations according to the invention may be contained in a wide variety of cosmetic preparations. Especially the following preparations, for example, come into consideration:
skin-care preparations, e.g. skin-washing and cleansing preparations in the form of tablet-form or liquid soaps, soapless detergents or washing pastes;
bath preparations, e.g. liquid (foam baths, milks, shower preparations) or solid bath preparations, e.g. bath cubes and bath salts;
skin-care preparations, e.g. skin emulsions, multi-emulsions or skin oils;
cosmetic personal care preparations, e.g. facial make-up in the form of day creams or powder creams, face powder (loose or pressed), rouge or cream make-up, eye-care preparations, e.g. eyeshadow preparations, mascara, eyeliner, eye creams or eye-fix creams; lip-care preparations, e.g. lipsticks, lip gloss, lip contour pencils, nail-care preparations, such as nail varnish, nail varnish removers, nail hardeners or cuticle removers;
intimate hygiene preparations, e.g. intimate washing lotions or intimate sprays;
foot-care preparations, e.g. foot baths, foot powders, foot creams or foot balsams, special deodorants and antiperspirants or callous-removing preparations;
light-protective preparations, such as sun milks, lotions, creams and oils, sun blocks or tropicals, pre-tanning preparations or after-sun preparations;
skin-tanning preparations, e.g. self-tanning creams;
depigmenting preparations, e.g. preparations for bleaching the skin or skin-lightening preparations;
insect-repellents, e.g. insect-repellent oils, lotions, sprays or sticks;
deodorants, such as deodorant sprays, pump-action sprays, deodorant gels, sticks or roll-ons;
antiperspirants, e.g. antiperspirant sticks, creams or roll-ons;
preparations for cleansing and caring for blemished skin, e.g. soapless detergents (solid or liquid), peeling or scrub preparations or peeling masks;
hair-removal preparations in chemical form (depilation), e.g. hair-removing powders, liquid hair-removing preparations, cream- or paste-form hair-removing preparations, hair-removing preparations in gel form or aerosol foams;
shaving preparations, e.g. shaving soap, foaming shaving creams, non-foaming shaving creams, foams and gels, preshave preparations for dry shaving, aftershaves or after-shave lotions;
fragrance preparations, e.g. fragrances (eau de Cologne, eau de toilette, eau de parfum, parfum de toilette, perfume), perfume oils or cream perfumes;
dental-care, denture-care and mouth-care preparations, e.g. toothpastes, gel tooth-pastes, tooth powders, mouthwash concentrates, anti-plaque mouthwashes, denture cleaners or denture fixatives;
cosmetic hair-treatment preparations, e.g. hair-washing preparations in the form of shampoos and conditioners, hair-care preparations, e.g. pretreatment preparations, hair tonics, styling creams, styling gels, pomades, hair rinses, treatment packs, intensive hair treatments, hair-structuring preparations, e.g. hair-waving preparations for permanent waves (hot wave, mild wave, cold wave), hair-straightening preparations, liquid hair-setting preparations, foams, hairsprays, bleaching preparations; e.g. hydrogen peroxide solutions, lightening shampoos, bleaching creams, bleaching powders, bleaching pastes or oils, temporary, semi-permanent or permanent hair colourants, preparations containing self-oxidising dyes, or natural hair colourants, such as henna or camomile.
An antimicrobial soap has, for example, the following composition:
0.01 to 5% by weight of the compound of formula (1)
0.3 to 1% by weight titanium dioxide
1 to 10% by weight stearic acid
ad 100% soap base, e.g. the sodium salts of tallow fatty acid and coconut fatty acid or glycerol.
A shampoo has, for example, the following composition:
0.01 to 5% by weight of the compound of formula (1)
12.0% by weight sodium laureth-2-sulfate
4.0% by weight cocamidopropyl betaine
3.0% by weight NaCl and
water ad 100%.
A deodorant has, for example, the following composition:
0.01 to 5% by weight of the compound of formula (1)
60% by weight ethanol
0.3% by weight perfume oil and
water ad 100%.
The invention relates also to an oral composition, comprising from 0.01 to 15% by weight, based on the total weight of the composition, of the compound of formula (1), and orally tolerable adjuvants.
Example of an oral composition:
10% by weight sorbitol
10% by weight glycerol
15% by weight ethanol
15% by weight propylene glycol
0.5% by weight sodium lauryl sulfate
0.25% by weight sodium methylcocyl taurate
0.25% by weight polyoxypropylene/polyoxyethylene block copolymer
0.10% by weight peppermint flavouring
0.1 to 0.5% by weight of a compound of formula (1) and
48.6% by weight water.
The oral composition according to the invention may be, for example, in the form of a gel, a paste, a cream or an aqueous preparation (mouthwash).
The oral composition according to the invention may also comprise compounds that release fluoride ions which are effective against the formation of caries, for example inorganic fluoride salts, e.g. sodium, potassium, ammonium or calcium fluoride, or organic fluoride salts, e.g. amine fluorides, which are known under the trade name Olafluor.
The oxathiazolones of formula (1) used according to the invention are also suitable for the treatment of textile fibre materials. Such materials are undyed and dyed or printed fibre materials, e.g. of silk, wool, polyamide or polyurethanes, and especially cellulosic fibre materials of all kinds. Such fibre materials are, for example, natural cellulose fibres, such as cotton, linen, jute and hemp, as well as cellulose and regenerated cellulose. Preferred suitable textile fibre materials are made of cotton.
The oxathiazolones of formula (1) are also used in washing and cleaning formulations, e.g. in liquid or powder washing agents or softeners.
The oxathiazolones used according to the invention are also suitable for imparting anti-microbial properties to plastics, e.g. polyethylene, polypropylene, polyurethane, polyester, polyamide, polycarbonate, latex etc. Fields of use therefor are, for example, floor coverings, plastics coatings, plastics container and packaging materials, kitchen and bathroom utensils (e.g. brushes, shower curtains, sponges, bathmats), latex filter materials (air and water filters), plastics articles used in the field of medicine, e.g. dressing materials, syringes, catheters etc., so-called xe2x80x9cmedical devicesxe2x80x9d, gloves and mattresses.
Paper, for example papers used for hygiene purposes, may also be provided with anti-microbial properties using the oxathiazolones according to the invention.
It is also possible for nonwovens, e.g. nappies/diapers, sanitary towels, panty liners, and cloths for hygiene and household uses, to be provided with antimicrobial properties in accordance with the invention.
The oxathiazolones can be used especially also in household and all-purpose cleaners for cleaning and disinfecting hard surfaces.
A cleaning preparation has, for example, the following composition:
0.01 to 5% of the compound of formula (1)
3.0% octyl alcohol 4EO
1.3% fatty alcohol C8-C10polyglucoside
3.0% isopropanol
ad 100% water.
In addition to preserving cosmetic and household products, technical products, such as paper treatment liquors, printing thickeners of starch or of cellulose derivatives, surface-coatings and paints, can be preserved and provided with antimicrobial properties.
The oxathiazolones of formula (1) are also suitable for the antimicrobial treatment of wood and for the antimicrobial treatment of leather and the provision of leather with antimicrobial properties.
The compounds according to the invention are also suitable for the protection of cosmetic products and household products from microbial damage.
The following Examples serve to illustrate the invention but do not limit the invention to the Examples.